I don’t know about you, but I often have a hard time trying to figure out what to wear for an evening event, like a cocktail party or a black-tie dinner. Do I wear a dress that I’d wear to a wine tasting to a cocktail party? Would something that I’d wear to the opera work for a black-tie dinner? I usually end up trying on practically every outfit in my closet while trying to imagine if I’ll fit in with the other guests. So, in order to help you avoid the pitfalls of not knowing what to wear to three key evening affairs — black-tie dinners, cocktail parties, and wine tastings — I’ve done a bit of research and created this list of do’s and don’ts for success:

Black-Tie Dinner

If you plan to be at a formal dinner where the men will be dressed like Cary Grant, think Jackie Kennedy in a sleeveless, floor-length dinner dress with a full or fitted skirt. Then again, a shorter, glamorous dress or dressy pants will work, too. Dress like a Grecian goddess with a dress with beautiful draping. Dress like Jackie, Michelle Obama, or Victoria Beckham in a classic sheath dress. Imagine the type of outfit Audrey Hepburn would cloak herself in. If you decide to wear separates, make sure your top is tailored and has some flair. Show your shoulders off but don’t reveal too much bosom. Wear high heels with straps, and add a glittery wrap for that extra elegant touch. Your best jewelry is a must.

Cocktail Party

Whether you’re drinking something shaken–not stirred, or a GoldFinger, if you wear a sleek cocktail dress or a sequined tunic and silky pants, you’ll fit right in. Think cool elegance. Think Audrey Hepburn and Grace Kelly. The key to a great cocktail look is the fabric—the more luxurious the better. Now is the time to wear something in silk, velvet, tulle, chiffon, or brocade. You won’t go wrong if you wear a little black dress. Remember The Great Gatsby era and add some ruffles, sequins, beading, or feathers to look like a modern Daisy Buchanan. Traditional cocktail dresses with hems that fall just above the knee or ankle are always acceptable and these days; your hem can fall as high or low as you’d like. Stiletto heels will give you height and make your legs look longer and thinner. For a more casual cocktail party, a maxi-dress and flats or sandals will do the trick.

Wine Tasting

Wine tastings are the epitome of the elite evening event. Whether you’re at a boutique winery in the Napa Valley or a wine bar in London, dressing for a wine tasting requires taste, sophistication, and understatement. A simple tunic with wide-legged pants in silk or diaphanous cotton will work as will a natural fiber knit top worn over leggings. To complete the look, wear a sophisticated scarf, large jewelry pieces, and sandals or flats (unless you’re in the Rockies or Napa, where riding boots are the norm).